This paper exemplifies several methods for retrofitting existing housing through four case studies, representative of the historical centre of Enna, a small town in Sicily, according to the requirements of static safety, typological adaptation and indoor comfort. These buildings were mostly built in the nineteenth century, up to three floors based on load-bearing masonry, iron joists and hollow tile floors and wooden roofs. A typological and construction analysis of these buildings was carried out to identify the stratigraphy of the different technical elements. Static and energy audits had been previously undertaken to understand the gap between the current state of the buildings and Italian standards and to develop appropriate interventions taking into account the site characteristics and the energy and seismic risk class pre-and post-retrofit intervention. The analyses and the retrofit interventions were performed in compliance with Italian standards and laws and strove to reach the minimum level. The study supports the planning of structural and energy retrofit interventions designed for historic load-bearing masonry buildings. Finally, the study simulates a strategy of action to provide subsidies and tax relief related to effective seismic and/or energy improvement that could be relevant for owners/builders as well as for local authorities.